Menthylated oil of wintergreen.



UNITED s r' GUSTAV BLIEBERGER, OF NEW YORK. N. Y.

MENTHYLATED 01L 0? WINTERGREEN.

No Drawing. Application filed April 27,

To all whom it may concern:

Be it known that I, Grrsrav BLIEBERGER/t citizen of the Empire of Austria-Hungary, and a resident of New York, in the county and State of New York, have invented a new and useful Chemical Compound. the lllcnthylated, Oil of Wintergreen, and the Process of Producing Same.

As well known, the oil of Wintergreen orthe oil of Gm/Zt/iera'a' prom/moons consists almost wholly of the inethylic ester otthe salicylic: acid which combines directly with metallic bases such as potassium. barium andthe like because it contains a hydroxyl group as is apparent from its constitutional form ul a.

Ol-l.C ILCO .CH

This indicates that condensation with organic radicals may also be possible. Mcnthol likewise possesses a hydroxyl group as is seen from its constitutional tormula The action of menthol. towa 'd acetic acid when beginning to .t'orm acetate of menthol shows the action of secondary alcohols. Thus the principal constituent of the oil of 'wintergreeu forms combinations with bases practically like an organic acid and the menthol shows the characteristics of an alcohol whereby all. the conditions are given for producing a new chemical compound which is supposed to he an ester.

The well known medicinal properties of the two components used for producing; the new chemical compound need not be"described here. It is self evident that the new compound possesses the conil'iined beneficial properties of both substances to a certain eX-' tent whereby a compound is produced particularly well adapted for instance as a resorbenf of uric acid in the system. The transformation of the two substances or their condensation is not easily ei'lected. However I have discovered that the transformation into a compound ether gradually effected when both substances are heated under the pressure of carbonic acid ga for rather a very long time at a temperature approaching nearly the boiling point of the oil of Wintergreen.

In carrying the invention into etl'ect l; substantially proceed as follows: About enact-ion Specification of Letters Fatent.

'Patented Dec. 27, rain.

1910. Serial No. 557,866.

equal parts of oil of Wintergreen and men-.

ents of which are so selected that heat over 200 C. may be produced thereby. The heating is eli'cctcd in an atmosphere of carbon dioxid, the closed vessel being in connection with a cylinder containing liquid carbonic acid gas so that there is a carbon dioxid atmosphere under pressure within the vessel while heating. According to the quantities employed the heating is continued for various lengths of time. for from 72 to 100 hours. At any rate the transformation into an ester or the condensation of'the two substances progresses very slowly, evidently under separation of one molecule of water. When the substances have combined the mixture is allowed to cool sufiiciently to be transferred into a distillation apparatus and heated in a suitable bath somewhat higher than before, to 275 (1, in a partial vacuum until the new compound distils over. The partial vacuum is created by means of a suitable suction device which first takes out the air and then part of the vapors so that there is a pressure of about 18 inches within the vessel. The distillate is collected in a suitable vessel and represents a yellowish brown liquid of oily consistencv which is somewhat turbid .or cloudy. In order to purify the new product it IS poured over solid caustic soda and stirred and at once other. chloroform and fatty oils and has a specificgravity of 1.03709 at about 29 C. It passes over ata temperature or 255 to Q 1 be taken 265- C. i/Vheii, cliloiric oi ironieaddedthe product becomes red, v.

The new compound is a beneficial remedy against them} m, gout? arid the like Well adapted for re orbing uric acid in the sysifenh; it maybe. applied externally by rubbing the afi'ectecl limbs'preferahlym xe-i i suitable vehicle or internally mgeletin apsulee containing one-half gram,

three tiiiies a slay. I claim asmy'iiiventicnz v .1. The process of producing"menthylutetl oil of Wintergreen consisting in coupling menthol end 'oilof Wintergreen by heating the-in iii 'an atmosphere of carbon dioxicl un denpressure', ancl distilling the resulting product. v I

2. The process; of producing menthylatecl oil of Wintergreen consisting in coupling mentholand .oil o f wintergreeilby heating same for relatively long time in an atmosphere of carbon oli (1 under pressure at a pemtui-e slightly below the. boiling point the oil of wiiitei'gieen, and distilling the resulting product in a partial Vacuum.

of April, 1910.

3. The process of pioducii g inenthylatecl oil of \\'11'1tergree11 consisting in coupling menthol and oil of Wintergreen by heating some iii an atmosphere of carbon dioxid under pressure to a temperature slightly below the boiling of the Oil of Wintergreen, d1st1'l-' ling the resulting product in a; partial Vac- .uum, purifying the distillate by placing it in contact. with solid caustic soda, and filtering same.

TY in.

. this Zoth tloy GUSTAV it'nesses; w h

LUDWIG K. B51111,

,n 1971 Goblin u. lto mmi.

CID 

